You wrote: "But living in CV doesn't help because while I really don't want to be like so many other CV folks, I really don't want my kid to grow up with esteem issues that may happen if I don't at least partly play the game. So, I'm going to have to figure out this one."
… and i couldnt agree more. I grew up right there in that area, went to TPHS. It was actually pretty difficult when most kids had cars (brand new or drove their parents BMWs and even a Maserati) at 16, had Rolex watches, went "shopping" for fun and spent hundreds and hundreds of $$ while I stood by feeling completely weak and passive (I didnt know I was learning an excellent lesson), etc. My brother lives there now and is frugal, his daughter suffers and struggles with his 'rules' about spending.
I was so immature that i thought the reason we didnt have money was because my mother didnt work hard enough. I seriously resented her for it. She was single with FIVE children. Three in college at the time I remember thinking this way (did I already mention how immature I was???).
Anyway, this exact issue is another of the BIG REASONS we decided to pack up and leave San Diego in '02, at least for the school months of the year. The materialistic atmosphere was just getting worse and worse. Happily, it is not an issue here.